Luxury homes for sale & real estate in Roslindale, MA

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3D WALKTHROUGH

ABOUT THIS HOME
Luxury Home for sale in Roslindale, MA:
A rare new construction home in Roslindale, meticulously crafted by a local luxury builder and thoughtfully designed by * Kerry Driscoll Design * . This stunning residence showcases 3 levels of living boasting a bright, open design plan with upgraded wide-plank white oak flooring throughout, a designer kitchen with custom cabinetry, bar area w/ bev cooler, gas fp lv room with marble mantle and built-ins and a sunroom that seamlessly extends to a outdoor patio complete with a gas line for grilling, perfect for entertaining. The upper level offers 4 bedrooms including a serene primary suite featuring a spa-inspired bath with solid stone flooring and shower, stylish fixtures and a massive wa

$1,395,000

4 beds2.5 baths3,015 sq ft

415 Poplar St, Roslindale, MA 02131

Designer kitchen • Primary suite • Outdoor patio

ABOUT THIS HOME
Luxury Home for sale in Roslindale, MA:
INVESTORS and END-USERS! UNIQUE OPPORTUNITY to own a TRIPLE DECKER w/ ATTACHED AND VERSATILE ANNEX situated on Two Sizable Lots! Well-maintained and spacious, these units have a variety of features including Hardwood Floors, High Ceilings, Beautiful Woodwork, Pantries, Built-In Hutches, Stained Glass, French Doors, Ceiling Fans, Recessed Lighting & Rear Decks. There are 3 NEW, HIGH EFFICIENCY HEAT UNITS. The Basement has plenty of storage and Common Laundry. Also included are separate utilities & 3 off-street parking. The MODERN Two-Level ANNEX has great flexibility as an Art Studio, Meeting Room, Office, Gym, Rec Room or Bonus Room for guests, nannies, or family. It's is equip

$2,150,000

8 beds4 baths4,562 sq ft

26 Tower St, Jamaica Plain, MA 02130

Triple decker • Two sizable lots • Pantries

3D WALKTHROUGH

ABOUT THIS HOME
Luxury Home for sale in Roslindale, MA:
Modern luxury meets unbeatable location in this custom-built showstopper just minutes from Roslindale Village, Centre Street, and the Commuter Rail. Originally crafted as the builder’s own home, it’s loaded with high-end finishes, smart Lutron Caseta lighting, and sleek contemporary style throughout. The open layout is all about flow—perfect for entertaining and effortless everyday living. A chef’s kitchen with custom cabinetry connects to a sunlit dining area and opens through French doors to a huge patio and private garden—your dream setup for indoor/outdoor living. Downstairs offers a flexible bedroom suite or media room with garden views. Upstairs, the spa-

$1,225,000

4 beds3 baths2,539 sq ft

276 Cornell St, Roslindale, MA 02131

Custom cabinetry • Huge patio • High end finishes

NEW CONSTRUCTION

ABOUT THIS HOME
Luxury Home for sale in Roslindale, MA:
Multi-family to be built in 2026 by seller for advertised price including land and all hard costs of construction. All income and expense information is estimated for marketing purposes only. Purchaser to do their own due diligence. This approved parcel comes with fully designed and approved plans for a 9-unit development, featuring 8 sleek studio apartments above a prime commercial space. With a permit delivered at closing, the project will be shovel-ready and set for construction to begin in 2026. Don’t miss this rare opportunity to bring a high-demand development to market! Proposal in hand from local contractor who is prepared to build the project should buyers be interested.

$3,100,000

8 beds8 baths7,312 sq ft

579 American Legion Hwy, Boston, MA 02131

3,791 sq ft lot • 2 parking spots • Community pool

ABOUT THIS HOME
Luxury Home for sale in Roslindale, MA:
Looking for a strong investment? Welcome to Hemman Street - a rare opportunity in Roslindale. Currently operating at a mid–6% cap rate, this partially updated 3-family features modern, condo-quality finishes in Units 1 and 2, while Unit 3, though unrenovated, is leased at a strong rental rate through 8/31/2026. Units 1 and 2 offer updated kitchens and baths, hardwood floors, private outdoor space, and in-unit conveniences that appeal to today’s renters. Unit 3 provides excellent long-term value with its high existing income stream. Situated on a residential street minutes from Roslindale Village, the commuter rail, shops, and dining, this property delivers strong cash flow, turn

$1,125,000

5 beds3 baths2,318 sq ft

5 7 Hemman St, Roslindale, MA 02131

Fully renovated • In-unit conveniences • Updated kitchens

Property at 103-105 Neponset Ave, Roslindale, MA 02131, 6 beds, 4.5 baths

$1,325,000

6 beds4.5 baths2,640 sq ft

103-105 Neponset Ave, Roslindale, MA 02131

Property at 29 Paine, Boston, MA 02131, 4 beds, 2.5 baths

$1,199,000

4 beds2.5 baths4,022 sq ft

29 Paine, Boston, MA 02131

Property at 34 Averton St, Roslindale, MA 02131, 9 beds, 3 baths

$1,549,900

9 beds3 baths4,393 sq ft

34 Averton St, Roslindale, MA 02131

Property at 55 Metropolitan Ave, Roslindale, MA 02131, 5 beds, 3.5 baths

$995,000

5 beds3.5 baths2,622 sq ft

55 Metropolitan Ave, Roslindale, MA 02131

Property at 142 Metropolitan Unit A, Roslindale, MA 02131, 4 beds, 3 baths

$989,000

4 beds3 baths1,950 sq ft

142 Metropolitan Unit A, Roslindale, MA 02131

Property at 142 Birch St, Roslindale, MA 02131, 8 beds, 5 baths

$2,095,000

8 beds5 baths4,200 sq ft

142 Birch St, Roslindale, MA 02131

Property at 75 Glendower Rd, Roslindale, MA 02131, 9 beds, 4 baths

$1,299,000

9 beds4 baths4,248 sq ft

75 Glendower Rd, Roslindale, MA 02131

Property at 142 Birch St #2, Roslindale, MA 02131, 4 beds, 3.5 baths

$1,049,000

4 beds3.5 baths2,013 sq ft

142 Birch St #2, Roslindale, MA 02131

Property at 142 Birch St #1, Roslindale, MA 02131, 4 beds, 3.5 baths

$1,049,000

4 beds3.5 baths2,013 sq ft

142 Birch St #1, Roslindale, MA 02131

Property at 46 Belgrade Ave #2, Roslindale, MA 02131, 2 beds, 2 baths

$869,900

2 beds2 baths1,176 sq ft

46 Belgrade Ave #2, Roslindale, MA 02131

Property at 25 Crandall St, Roslindale, MA 02131, 6 beds, 2 baths

$949,900

6 beds2 baths2,308 sq ft

25 Crandall St, Roslindale, MA 02131

Property at 242 Belgrade Ave, Roslindale, MA 02131, 7 beds, 3 baths

$1,425,000

7 beds3 baths3,795 sq ft

242 Belgrade Ave, Roslindale, MA 02131

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ABOUT THIS HOME
Luxury Home for sale in Roslindale, MA:
Rare mixed-use opportunity (or building) in the heart of JP’s vibrant South Street corridor. This three-unit condo building features an established anchor business operating since 2004. a full-service bakery/café with a licensed 20x20 patio, and two spacious 4-bedroom residential units with covered porches. The property offers flexible use and strong income potential with projected rents of 15–18k monthly with the business in place. The commercial level features a walk-in freezer and an enormous high-ceiling basement with potential for restaurant or commercial expansion. Updated electrical with 400-amp service, FHA gas heat, and the option to dissolve the business and del

$2,900,000

8 beds2.5 baths3,996 sq ft

55 South St, Jamaica Plain, MA 02130

Full-service bakery • Licensed patio • 4,125 sq ft lot

ABOUT THIS HOME
Luxury Home for sale in Roslindale, MA:
Stunning two family with seven bedrooms, spacious living areas, quartz countertops and gleaming hardwood floors. This bright and airy home offers a unique opportunity to own a home on Wellington Hill minutes to Roslindale Center in a vibrant location that is close to shopping, the T station, and Bus route. Do not miss out!

$949,000

7 beds2 baths2,471 sq ft

30-32 Westmore Rd, Mattapan, MA 02126

Quartz countertops • Close to bus route • Close to t station

ABOUT THIS HOME
Luxury Home for sale in Roslindale, MA:
Beautifully maintained two-family home perched atop a quiet hill in Roslindale. Each unit offers 5 rooms, including 2 bedrooms and 1 bath, with hardwood floors throughout and an inviting, well-kept feel. The property also features a finished basement with private side entrance, full bath, kitchen, and living room—ideal for extended family, guests, or additional living space. Enjoy a landscaped yard perfect for relaxing or entertaining, plus off-street parking. Conveniently located near the George Wright Golf Course and Stony Brook Reservation, offering easy access to outdoor recreation while still close to city amenities. A wonderful opportunity for owner-occupants or investors seekin

$900,000

4 beds2 baths2,145 sq ft

23 Weeks Ave, Roslindale, MA 02131

Finished basement • Landscaped yard • Off-street parking

ABOUT THIS HOME
Luxury Home for sale in Roslindale, MA:
Collecting rents from Dec. Discover this beautifully updated 2-family home in one of Milton’s most desirable locations! This spacious three-story property is perfect for both investors and owner-occupants. The first floor has been fully renovated, showcasing a modern kitchen with stainless steel appliances, quartz countertops, and a bright open layout. The second unit extends across two levels, with generous bedrooms, ample storage, and a third-floor bonus retreat featuring a wet bar—ideal for entertaining or creating a private suite. Location highlights: set on Brush Hill Rd, the home offers quick access to I-93, making commutes to Boston and Cambridge effortless. Enjoy proximi

$1,295,000

8 beds4 baths2,785 sq ft

112 Brush Hill Rd, Milton, MA 02186

Quartz countertops • Bright open layout • Modern kitchen

ABOUT THIS HOME
Luxury Home for sale in Roslindale, MA:
Located at 12 Hiawatha, Boston, MA, this multi-family residence presents a unique opportunity to own a substantial property in this vibrant city. This building, constructed in 1905, holds immense potential. With a generous 4989 square feet of living area spread across four stories, the residence offers ample space for a variety of living arrangements. The 16 bedrooms provide comfortable accommodation, while the six full bathrooms ensure convenience for all occupants. The 7504 square feet lot area provides space and possibilities. This multi-family residence, steeped in history and brimming with potential, awaits your vision to transform it into a remarkable urban haven. From the moment you

$2,220,000

16 beds6 baths4,989 sq ft

12 Hiawatha, Mattapan, MA 02126

7,504 sq ft lot • Built 1905 • Listed 15 days

ABOUT THIS HOME
Luxury Home for sale in Roslindale, MA:
Stately & sprawling two family in highly desirable Milton location abutting the Columbines. 214 Brook Road offers an unmatched opportunity for the savvy buyer. Live multi-generational and owner occupy, off-set you mortgage payment with a tenant or hold as an investment opportunity with a promising return. Both units are in excellent condition, freshly painted and floors re-finished. High ceilings, classic woodwork, updated full baths and kitchens w/ white cabinetry, granite/stainless appliances and in-unit laundry. The fireplaced living room blends seamlessly into the dining room and kitchen, offering an open flow. Three generous bedrooms are buffered from the main living area by a sp

$1,349,999

7 beds3 baths3,443 sq ft

214 Brook Rd, Milton, MA 02186

Vaulted ceiling • In-unit laundry • Dining room

Property at 157-167 Delhi St, Mattapan, MA 02126, 33 beds, 18 baths

$5,700,000

33 beds18 baths15,744 sq ft

157-167 Delhi St, Mattapan, MA 02126

Property at 55 Redlands Rd, West Roxbury, MA 02132, 4 beds, 2.5 baths

$1,200,000

4 beds2.5 baths2,123 sq ft

55 Redlands Rd, West Roxbury, MA 02132

Property at 27 Havelock St, Dorchester, MA 02124, 11 beds, 3 baths

$1,299,000

11 beds3 baths3,930 sq ft

27 Havelock St, Dorchester, MA 02124

Property at 29 Havelock St, Dorchester, MA 02124, 11 beds, 3 baths

$1,299,000

11 beds3 baths3,930 sq ft

29 Havelock St, Dorchester, MA 02124

Property at 25 Fessenden St, Mattapan, MA 02126, 9 beds, 3 baths

$1,249,000

9 beds3 baths3,564 sq ft

25 Fessenden St, Mattapan, MA 02126

Property at 23 Fessenden St, Mattapan, MA 02126, 9 beds, 3 baths

$1,249,000

9 beds3 baths3,699 sq ft

23 Fessenden St, Mattapan, MA 02126

Property at 14 Starling St, West Roxbury, MA 02132, 4 beds, 2.5 baths

$1,625,000

4 beds2.5 baths2,700 sq ft

14 Starling St, West Roxbury, MA 02132

Property at 10 Sutton St, Mattapan, MA 02126, 12 beds, 3 baths

$1,350,000

12 beds3 baths3,894 sq ft

10 Sutton St, Mattapan, MA 02126

Property at 50 Heron St, West Roxbury, MA 02132, 3 beds, 2.5 baths

$1,169,000

3 beds2.5 baths2,064 sq ft

50 Heron St, West Roxbury, MA 02132

Property at 1125 W Roxbury Pkwy, Chestnut Hill, MA 02467, 4 beds, 3 baths

$2,799,000

4 beds3 baths3,859 sq ft

1125 W Roxbury Pkwy, Chestnut Hill, MA 02467

Property at 755-759 Truman Hwy, Hyde Park, MA 02136, 7 beds, 5 baths

$2,000,000

7 beds5 baths4,380 sq ft

755-759 Truman Hwy, Hyde Park, MA 02136

Property at 12 Eagle St, West Roxbury, MA 02132, 3 beds, 2 baths

$1,099,900

3 beds2 baths2,325 sq ft

12 Eagle St, West Roxbury, MA 02132

Property at 141 Beacon St, Hyde Park, MA 02136, 5 beds, 2.5 baths

$1,195,000

5 beds2.5 baths3,507 sq ft

141 Beacon St, Hyde Park, MA 02136

Property at 41 Jamaica St, Jamaica Plain, MA 02130, 4 beds, 3 baths

$1,495,000

4 beds3 baths2,601 sq ft

41 Jamaica St, Jamaica Plain, MA 02130

Luxury Homes for Sale in Roslindale

There are currently 17 luxury homes for sale in Roslindale at a median listing price of $689K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Roslindale stay on the market for 40 days and receive 2 offers. Popular neighborhoods include Hyde Park, Dorchester, Jamaica Plain, Chestnut Hill, and West Roxbury. This map is refreshed with the newest listings in Roslindale every 15 minutes.

In the past month, 30 homes have been sold in Roslindale. In addition to houses in Roslindale, there were also 65 condos, 13 townhouses, and 17 multi-family units for sale in Roslindale last month. Find your dream home in Roslindale using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in Roslindale are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Roslindale. If you're looking to sell your home in the Roslindale area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Roslindale with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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